1,3-Bis(2-anilino-2-oxoeth-yl)-1H-imidazol-3-ium chloride.

In the cation of the title salt, C(19)H(19)N(4)O(2) (+)·Cl(-), the dihedral angles between the imidazole ring and the phenyl rings are 70.39 (8) and 86.26 (9)°. The chloride anion inter-acts with the cation through an N-H⋯Cl hydrogen bond. In the crystal, classical N-H⋯O hydrogen bonds link the cations into chains parallel to the b axis. Non-classical C-H⋯Cl and C-H⋯O hydrogen bonds further connect the chains into a three-dimensional network.

Related literature

For the crystal structure of an acetonitrile monosolvate deriv­ative of the title compound, see: Liao & Lee (2011 ▶). For the crystal structures of nickel, palladium, and silver complexes with ligands derived from the title compound, see: Liao, Chan, Chang et al. (2007 ▶); Liao, Chan, Zeng et al. (2007 ▶); Liao et al. (2008 ▶).

Experimental

Crystal data

C19H19N4O2 +·Cl−

M = 370.83

Monoclinic,

a = 8.4375 (5) Å

b = 12.0446 (7) Å

c = 17.5449 (10) Å

β = 90.789 (3)°

V = 1782.85 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 150 K

0.11 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.975, T max = 0.984

11822 measured reflections

3684 independent reflections

1924 reflections with I > 2σ

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.096

S = 0.92

3684 reflections

311 parameters

All H-atom parameters refined

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: DIAMOND (Brandenburg, 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027110/rz2771sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027110/rz2771Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027110/rz2771Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H19N4O2+·Cl−	F(000) = 776
Mr = 370.83	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1122 reflections
a = 8.4375 (5) Å	θ = 2.9–18.5°
b = 12.0446 (7) Å	µ = 0.24 mm−1
c = 17.5449 (10) Å	T = 150 K
β = 90.789 (3)°	Prism, colourless
V = 1782.85 (18) Å3	0.11 × 0.09 × 0.07 mm
Z = 4

Bruker SMART APEXII diffractometer	3684 independent reflections
Radiation source: fine-focus sealed tube	1924 reflections with I > 2σ
Graphite monochromator	Rint = 0.062
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.975, Tmax = 0.984	k = −11→15
11822 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	All H-atom parameters refined
S = 0.92	w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
3684 reflections	(Δ/σ)max = 0.004
311 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.2603 (3)	0.6481 (2)	0.34316 (15)	0.0272 (6)
C2	0.3583 (3)	0.5510 (2)	0.24844 (14)	0.0311 (6)
C3	0.2750 (3)	0.6355 (2)	0.21849 (16)	0.0320 (7)
C4	0.1131 (3)	0.7918 (2)	0.26932 (16)	0.0302 (6)
C5	0.1673 (3)	1.0668 (2)	0.17161 (13)	0.0244 (6)
C6	0.2754 (3)	1.1355 (2)	0.20752 (15)	0.0306 (6)
C7	0.3198 (3)	1.2344 (2)	0.17338 (17)	0.0368 (7)
C8	0.2524 (3)	1.2655 (3)	0.10441 (17)	0.0449 (8)
C9	0.1429 (3)	1.1971 (2)	0.06952 (16)	0.0421 (8)
C10	0.1013 (3)	1.0980 (2)	0.10172 (14)	0.0331 (7)
C11	0.3070 (3)	0.3735 (2)	0.37508 (13)	0.0295 (6)
C12	0.3050 (3)	0.1740 (2)	0.40765 (12)	0.0283 (6)
C13	0.1423 (3)	0.1560 (2)	0.40360 (13)	0.0322 (7)
C14	0.0841 (4)	0.0495 (2)	0.41476 (14)	0.0392 (7)
C15	0.1843 (4)	−0.0380 (2)	0.42981 (14)	0.0405 (7)
C16	0.3452 (4)	−0.0205 (2)	0.43115 (14)	0.0386 (7)
C17	0.4066 (3)	0.0855 (2)	0.42045 (13)	0.0328 (7)
C18	0.2067 (3)	0.8904 (2)	0.23976 (13)	0.0274 (6)
C19	0.4067 (3)	0.4786 (2)	0.38240 (16)	0.0314 (7)
Cl1	0.26726 (7)	0.80315 (6)	0.03880 (3)	0.0388 (2)
H1	0.231 (2)	0.6733 (16)	0.3934 (11)	0.022 (6)*
H2	0.416 (3)	0.4943 (18)	0.2284 (12)	0.028 (7)*
H3	0.264 (3)	0.6624 (18)	0.1704 (13)	0.034 (7)*
H6	0.320 (3)	1.1175 (18)	0.2553 (12)	0.033 (7)*
H7	0.392 (3)	1.2781 (18)	0.2008 (12)	0.032 (7)*
H8	0.282 (3)	1.3315 (19)	0.0838 (13)	0.035 (7)*
H9	0.091 (3)	1.2152 (19)	0.0257 (13)	0.042 (8)*
H10	0.023 (2)	1.0480 (17)	0.0767 (11)	0.027 (6)*
H13	0.068 (3)	0.2155 (18)	0.3914 (11)	0.028 (6)*
H14	−0.026 (3)	0.0440 (19)	0.4129 (13)	0.043 (8)*
H15	0.139 (3)	−0.113 (2)	0.4405 (12)	0.039 (7)*
H17	0.522 (3)	0.1020 (18)	0.4243 (12)	0.038 (7)*
H18	0.424 (3)	−0.080 (2)	0.4398 (13)	0.052 (8)*
H3A	0.020 (3)	0.9449 (18)	0.1915 (13)	0.037 (8)*
H4A	0.487 (3)	0.2905 (19)	0.4204 (12)	0.044 (7)*
H19A	0.515 (3)	0.4632 (17)	0.3747 (11)	0.025 (7)*
H24A	0.072 (2)	0.8109 (17)	0.3210 (12)	0.029 (6)*
H19B	0.392 (3)	0.5105 (18)	0.4335 (13)	0.035 (7)*
H24B	0.025 (3)	0.7722 (17)	0.2349 (12)	0.029 (7)*
N1	0.3482 (2)	0.55995 (16)	0.32678 (11)	0.0268 (5)
N2	0.2136 (2)	0.69471 (16)	0.27795 (11)	0.0253 (5)
N3	0.1147 (3)	0.96669 (17)	0.20510 (11)	0.0286 (5)
N4	0.3760 (2)	0.28106 (17)	0.40204 (11)	0.0297 (5)
O1	0.34999 (19)	0.89706 (13)	0.25021 (9)	0.0334 (4)
O2	0.1733 (2)	0.37764 (14)	0.34706 (10)	0.0438 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0260 (15)	0.0289 (16)	0.0266 (15)	−0.0041 (12)	0.0008 (12)	0.0001 (13)
C2	0.0312 (16)	0.0303 (16)	0.0317 (16)	0.0086 (14)	0.0023 (13)	−0.0032 (14)
C3	0.0300 (16)	0.0372 (17)	0.0288 (15)	0.0026 (13)	0.0001 (13)	0.0056 (14)
C4	0.0237 (15)	0.0287 (16)	0.0384 (17)	0.0032 (13)	0.0004 (14)	0.0028 (14)
C5	0.0216 (13)	0.0228 (14)	0.0289 (14)	0.0005 (11)	0.0042 (12)	−0.0003 (12)
C6	0.0289 (15)	0.0280 (16)	0.0347 (17)	0.0020 (13)	0.0004 (14)	−0.0004 (13)
C7	0.0296 (16)	0.0288 (17)	0.0523 (19)	0.0011 (13)	0.0042 (15)	−0.0083 (15)
C8	0.0396 (18)	0.0392 (19)	0.056 (2)	−0.0003 (16)	0.0123 (16)	0.0167 (17)
C9	0.0372 (17)	0.050 (2)	0.0388 (17)	−0.0016 (16)	−0.0035 (15)	0.0133 (16)
C10	0.0300 (16)	0.0366 (17)	0.0326 (16)	−0.0007 (14)	−0.0001 (13)	−0.0004 (14)
C11	0.0252 (15)	0.0331 (16)	0.0302 (14)	0.0024 (13)	0.0006 (12)	0.0030 (12)
C12	0.0329 (16)	0.0292 (16)	0.0227 (13)	0.0001 (13)	0.0021 (12)	0.0023 (12)
C13	0.0336 (17)	0.0351 (18)	0.0279 (14)	−0.0003 (14)	−0.0019 (13)	0.0040 (13)
C14	0.0385 (19)	0.047 (2)	0.0322 (16)	−0.0070 (16)	−0.0050 (14)	0.0011 (14)
C15	0.054 (2)	0.0349 (19)	0.0322 (16)	−0.0101 (17)	−0.0051 (15)	0.0017 (14)
C16	0.051 (2)	0.0366 (18)	0.0284 (15)	0.0083 (16)	−0.0033 (14)	0.0005 (13)
C17	0.0341 (17)	0.0357 (18)	0.0287 (15)	0.0039 (14)	0.0023 (13)	0.0000 (13)
C18	0.0247 (15)	0.0299 (16)	0.0276 (14)	0.0002 (13)	0.0011 (12)	−0.0029 (12)
C19	0.0251 (17)	0.0349 (17)	0.0341 (17)	0.0027 (13)	−0.0054 (14)	0.0062 (14)
Cl1	0.0346 (4)	0.0441 (4)	0.0375 (4)	0.0001 (3)	−0.0066 (3)	−0.0045 (3)
N1	0.0215 (11)	0.0291 (13)	0.0298 (12)	0.0011 (10)	−0.0009 (9)	0.0033 (10)
N2	0.0231 (11)	0.0233 (11)	0.0297 (11)	0.0004 (10)	0.0004 (10)	0.0031 (10)
N3	0.0215 (13)	0.0295 (13)	0.0348 (12)	−0.0016 (11)	−0.0041 (11)	0.0045 (10)
N4	0.0230 (12)	0.0335 (14)	0.0325 (12)	0.0013 (11)	−0.0047 (10)	0.0044 (11)
O1	0.0239 (10)	0.0311 (10)	0.0451 (11)	−0.0004 (8)	−0.0039 (9)	0.0031 (8)
O2	0.0294 (11)	0.0372 (12)	0.0644 (13)	−0.0015 (9)	−0.0159 (10)	0.0118 (9)

C1—N1	1.329 (3)	C10—H10	0.99 (2)
C1—N2	1.329 (3)	C11—O2	1.225 (3)
C1—H1	0.97 (2)	C11—N4	1.340 (3)
C2—C3	1.340 (3)	C11—C19	1.523 (3)
C2—N1	1.382 (3)	C12—C17	1.384 (3)
C2—H2	0.91 (2)	C12—C13	1.391 (3)
C3—N2	1.371 (3)	C12—N4	1.426 (3)
C3—H3	0.91 (2)	C13—C14	1.387 (4)
C4—N2	1.451 (3)	C13—H13	0.97 (2)
C4—C18	1.522 (3)	C14—C15	1.375 (4)
C4—H24A	1.00 (2)	C14—H14	0.93 (2)
C4—H24B	0.98 (2)	C15—C16	1.374 (4)
C5—C6	1.378 (3)	C15—H15	1.00 (2)
C5—C10	1.392 (3)	C16—C17	1.392 (4)
C5—N3	1.415 (3)	C16—H18	0.99 (3)
C6—C7	1.387 (3)	C17—H17	1.00 (2)
C6—H6	0.94 (2)	C18—O1	1.223 (3)
C7—C8	1.382 (4)	C18—N3	1.343 (3)
C7—H7	0.94 (2)	C19—N1	1.464 (3)
C8—C9	1.376 (4)	C19—H19A	0.94 (2)
C8—H8	0.91 (2)	C19—H19B	0.99 (2)
C9—C10	1.368 (4)	N3—H3A	0.87 (2)
C9—H9	0.91 (2)	N4—H4A	0.99 (2)
N1—C1—N2	108.1 (2)	C13—C12—N4	123.6 (2)
N1—C1—H1	126.8 (12)	C14—C13—C12	119.2 (3)
N2—C1—H1	125.1 (12)	C14—C13—H13	118.9 (13)
C3—C2—N1	107.0 (2)	C12—C13—H13	121.8 (13)
C3—C2—H2	134.2 (13)	C15—C14—C13	121.2 (3)
N1—C2—H2	118.8 (13)	C15—C14—H14	124.2 (15)
C2—C3—N2	107.3 (2)	C13—C14—H14	114.6 (15)
C2—C3—H3	133.2 (14)	C16—C15—C14	119.4 (3)
N2—C3—H3	119.0 (14)	C16—C15—H15	121.0 (13)
N2—C4—C18	111.1 (2)	C14—C15—H15	119.6 (14)
N2—C4—H24A	107.4 (12)	C15—C16—C17	120.5 (3)
C18—C4—H24A	108.4 (13)	C15—C16—H18	123.5 (15)
N2—C4—H24B	107.8 (13)	C17—C16—H18	116.0 (15)
C18—C4—H24B	111.7 (12)	C12—C17—C16	119.9 (3)
H24A—C4—H24B	110.3 (18)	C12—C17—H17	117.5 (13)
C6—C5—C10	119.6 (2)	C16—C17—H17	122.6 (13)
C6—C5—N3	122.1 (2)	O1—C18—N3	126.0 (2)
C10—C5—N3	118.2 (2)	O1—C18—C4	121.1 (2)
C5—C6—C7	120.0 (2)	N3—C18—C4	112.9 (2)
C5—C6—H6	121.5 (14)	N1—C19—C11	108.6 (2)
C7—C6—H6	118.6 (14)	N1—C19—H19A	110.7 (13)
C8—C7—C6	120.1 (3)	C11—C19—H19A	111.0 (13)
C8—C7—H7	123.8 (14)	N1—C19—H19B	107.5 (13)
C6—C7—H7	116.0 (14)	C11—C19—H19B	109.0 (13)
C9—C8—C7	119.5 (3)	H19A—C19—H19B	109.9 (18)
C9—C8—H8	122.1 (15)	C1—N1—C2	108.6 (2)
C7—C8—H8	118.3 (15)	C1—N1—C19	125.1 (2)
C10—C9—C8	120.9 (3)	C2—N1—C19	125.9 (2)
C10—C9—H9	115.8 (16)	C1—N2—C3	108.9 (2)
C8—C9—H9	123.3 (16)	C1—N2—C4	126.6 (2)
C9—C10—C5	119.9 (3)	C3—N2—C4	124.5 (2)
C9—C10—H10	121.3 (12)	C18—N3—C5	126.0 (2)
C5—C10—H10	118.8 (12)	C18—N3—H3A	116.1 (15)
O2—C11—N4	124.6 (2)	C5—N3—H3A	115.7 (15)
O2—C11—C19	120.3 (2)	C11—N4—C12	126.5 (2)
N4—C11—C19	115.1 (2)	C11—N4—H4A	115.0 (14)
C17—C12—C13	119.7 (2)	C12—N4—H4A	118.5 (13)
C17—C12—N4	116.6 (2)
N1—C2—C3—N2	−0.6 (3)	N2—C1—N1—C2	0.4 (3)
C10—C5—C6—C7	−1.0 (4)	N2—C1—N1—C19	−172.4 (2)
N3—C5—C6—C7	−178.1 (2)	C3—C2—N1—C1	0.1 (3)
C5—C6—C7—C8	1.8 (4)	C3—C2—N1—C19	172.8 (2)
C6—C7—C8—C9	−0.9 (4)	C11—C19—N1—C1	104.1 (3)
C7—C8—C9—C10	−0.8 (4)	C11—C19—N1—C2	−67.5 (3)
C8—C9—C10—C5	1.6 (4)	N1—C1—N2—C3	−0.8 (3)
C6—C5—C10—C9	−0.7 (4)	N1—C1—N2—C4	178.8 (2)
N3—C5—C10—C9	176.5 (2)	C2—C3—N2—C1	0.8 (3)
C17—C12—C13—C14	1.9 (4)	C2—C3—N2—C4	−178.7 (2)
N4—C12—C13—C14	−175.7 (2)	C18—C4—N2—C1	110.3 (3)
C12—C13—C14—C15	0.1 (4)	C18—C4—N2—C3	−70.2 (3)
C13—C14—C15—C16	−2.3 (4)	O1—C18—N3—C5	2.7 (4)
C14—C15—C16—C17	2.6 (4)	C4—C18—N3—C5	−179.6 (2)
C13—C12—C17—C16	−1.7 (4)	C6—C5—N3—C18	−45.1 (3)
N4—C12—C17—C16	176.1 (2)	C10—C5—N3—C18	137.8 (2)
C15—C16—C17—C12	−0.6 (4)	O2—C11—N4—C12	−4.3 (4)
N2—C4—C18—O1	−25.1 (3)	C19—C11—N4—C12	174.8 (2)
N2—C4—C18—N3	157.1 (2)	C17—C12—N4—C11	165.6 (2)
O2—C11—C19—N1	−22.6 (3)	C13—C12—N4—C11	−16.7 (4)
N4—C11—C19—N1	158.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.87 (2)	1.94 (2)	2.799 (3)	171 (2)
N4—H4A···Cl1ii	0.99 (2)	2.19 (2)	3.182 (2)	177.4 (19)
C1—H1···Cl1iii	0.97 (2)	2.58 (2)	3.482 (3)	155.0 (16)
C2—H2···O1ii	0.91 (2)	2.32 (2)	3.082 (3)	140.6 (17)
C13—H13···O2	0.97 (2)	2.29 (2)	2.862 (3)	116.9 (16)
C4—H24B···O2i	0.98 (2)	2.54 (2)	3.308 (3)	136.0 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.87 (2)	1.94 (2)	2.799 (3)	171 (2)
N4—H4A⋯Cl1ii	0.99 (2)	2.19 (2)	3.182 (2)	177.4 (19)
C1—H1⋯Cl1iii	0.97 (2)	2.58 (2)	3.482 (3)	155.0 (16)
C2—H2⋯O1ii	0.91 (2)	2.32 (2)	3.082 (3)	140.6 (17)
C13—H13⋯O2	0.97 (2)	2.29 (2)	2.862 (3)	116.9 (16)
C4—H24B⋯O2i	0.98 (2)	2.54 (2)	3.308 (3)	136.0 (16)

Symmetry codes: (i) ; (ii) ; (iii) .